"Can I Wear an Expensive Watch with Cheap Clothes?"

I've been fortunate enough in my career that I can splurge on an expensive watch (in my case, the object of desire is a Rolex). However, I am in a profession where I can literally work in shorts and a T-shirt. Is it acceptable to wear an expensive watch with completely inexpensive clothes?

Not only is it acceptable but in some eyes, such as mine, it may be preferable. If it's a Rolex Oyster you have your eye on, that's a sports watch, and depending on the model, it was designed for divers, yachtsmen, or aviators—not casino gamblers, tango dancers, or oenophiles. Rolex notes that the Oyster Perpetual Submariner, which is waterproof to 300 meters, was designed to fit over a light diving suit (not under a tails coat). The Explorer was the first watch worn to the top of Mount Everest, and it is popular among spelunkers. Contemporary watch aficionados often wear their sports watches with suits, and some have expressed the opinion that I'm an irrelevant fussbudget for thinking sports watches should be worn with leisure clothes and dress watches should be worn with suits. I am not a fussbudget. A chronic suit wearer looks better with a dressier watch, and if he wants a Rolex, that's why they make the Rolex Cellini, which was designed to fit not over a rubber suit but inside a wool one. Usually, a dress watch has fewer buttons and dials, and do I need to mention it should be seen and not heard? Any watch that plays "Für Elise" in a movie theater should be arrested.